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1. WO2020008340 - PROCÉDÉS DE PRÉPARATION DE COMPOSÉS (E)-(2-(CHLOROMÉTHYL)-3-FLUOROALLYL)CARBAMATES

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

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CLAIMS

1. A method of preparing a solid compound of Formula 1, the method comprising (a) refluxing a compound of Formula lc in an organic solvent to form a reaction mixture; and (b) crystallizing the reaction mixture by cooling to less than 20 °C to obtain the solid compound of Formula 1,

Boc (Formula 1)


Boc (Formula lc)

wherein Boc is a nitrogen protecting group.

2. The method of Claim 1, wherein said organic solvent is hexane, heptane, a mixed solvent of heptane and methyl ethyl ketone, a mixed solvent of heptane and toluene, a mixed solvent of heptane and methyl t-butyl ether, a mixed solvent of heptane and isopropyl alcohol, a mixed solvent of heptane and acetone, a mixed solvent of heptane and ethyl acetate, a mixed solvent of heptane and tetrahydrofuran, a mixed solvent of heptane and methyl isobutyl ketone, a mixed solvent of heptane and n-propanol, a mixed solvent of heptane and acetonitrile, a mixed solvent of heptane and isopropyl acetate, a mixed solvent of hexane and methyl ethyl ketone, a mixed solvent of hexane and toluene, a mixed solvent of hexane and methyl t-butyl ether, a mixed solvent of hexane and isopropyl alcohol, a mixed solvent of hexane and acetone, a mixed solvent of hexane and ethyl acetate, a mixed solvent of hexane and tetrahydrofuran, a mixed solvent of hexane and methyl isobutyl ketone, a mixed solvent of hexane and n-propanol, a mixed solvent of hexane and acetonitrile, or a mixed solvent of hexane and isopropyl acetate.

3. The method of Claim 1, wherein said organic solvent is used in a proportion of 3 mL-7 mL with respect to 1 g of the compound of Formula lc.

4. The method of Claim 1, wherein said refluxing is carried out at a temperature in the range of about 60 °C to about 80 °C.

5. The method of Claim 1, wherein Step (b) is carried out via crystallization by cooling the reaction mixture to a temperature in a range of about -10 °C to about 20 °C.

6. The method of Claim 1, wherein Step (b) is carried out via crystallization by cooling the reaction mixture for more than 1 hour.

7. The method of any one of Claims 1-6, wherein said compound of Formula lc is obtained by a method comprising (i) reacting a compound of Formula 3 with

tetrabutylammonium fluoride to provide a compound of Formula 2; and (ii) reacting said compound of Formula 2 with methanesulfonyl chloride in the presence of a base, followed by reaction with lithium chloride,


oc (Formula 3)

wherein Boc is a nitrogen protecting group and TBDMSO is tert-butyldimethylsilyloxy.

8. The method of Claim 7, wherein Step (ii) is carried out without isolating said compound of Formula 2 prepared in Step (i).

9. A compound of Formula 1,


Boc (Formula 1)

wherein Boc is a nitrogen protecting group and the compound is a solid.